Synthesis, DFT study, molecular docking and insecticidal evaluation of some pyrazole-based tetrahydropyrimidine derivatives

Abstract

The building block synthon, 1-(4-(1,3-diphenyl-1H-pyrazol-4-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethan-1-one was efficiently synthesized by Biginelli reaction of 1,3-diphenyl-1H-pyrazole-4-carbaldehdye, acetylacetone, and thiourea and submitted to react with ethyl chloroacetate and chloroacetyl chloride under different conditions to afford some N-heterocycles integrated with pyrazole scaffold. Hydrazinolysis of the pyrimidinethione was studied under different conditions. The insecticidal activity for these compounds, DFT calculations, and docking were run and discussed. Some of them exhibited 100% mortality against Nilaparvata lugens and Mythimna separata.

Graphical Abstract

Keywords:

• DFT
• docking
• insecticidal
• tetrahydropyrimidinethione
• thiazolopyrimidine

Acknowledgments

Technical supports from Chemistry Department, Faculty of Science, Ain Shams University and Aysel-lab in insect blocked company are gratefully acknowledged.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Correction Statement

This article has been republished with minor changes. These changes do not impact the academic content of the article.